OpenAI confidentially filed paperwork for an initial public offering Monday, joining Anthropic and Elon Musk‘s SpaceX in a wave of trillion-dollar listings expected to hit Wall Street within months.

But the ChatGPT maker may face a structural problem. If SpaceX and Anthropic exhaust investor appetite first, OpenAI could pay the discount on its debut.

SpaceX, which merged with Musk’s xAI earlier this year, prices Thursday at roughly $1.8 trillion, the biggest IPO ever. Anthropic filed last week at $965 billion. OpenAI makes three AI-adjacent listings in days.

The Bear Case Against Going Last

Bankers have warned Anthropic and OpenAI that whichever startup files first will benefit from deeper pools of investor cash, the Wall Street Journal reported. Lock-up periods on all three names will also expire roughly six months out, potentially triggering simultaneous insider selling.

NYU Stern professor Scott Galloway has gone further, assigning a “nonzero probability” earlier this year that OpenAI’s IPO gets pulled entirely. He has called the current IPO environment a “rigged game” in which opening prices will be “completely irrational.”

Hours after Anthropic’s filing, Chief Executive Sam Altman called corporate concern over excessive AI spending “fair criticism.”

Tufts University’s Bhaskar Chakravorti has calculated AI revenue would need $2 trillion annually by 2030 to justify compute commitments, implying an $800 billion shortfall.

Yardeni Research disagrees, noting the three AI listings are expected to raise roughly $200 billion combined against a Wilshire 5000 market cap of $75.6 trillion.

OpenAI’s Specific Problem

OpenAI reportedly missed certain internal revenue and user growth targets, and Anthropic recently surpassed it in private market valuation for the first time.

The company said in its filing statement that “it may be a while” before listing, with Altman framing the timing as a “financing event” rather than a race.

OpenAI may burn cash at a level that dwarfs any public company in history, per forecasts shared with investors and reported by the Wall Street Journal. Much of that spending flows to infrastructure suppliers, with Nvidia (NASDAQ:NVDA), an OpenAI investor and chip supplier, a clear beneficiary.

The Polymarket Angle

Polymarket traders are pricing the race directly, with the contract on whether Anthropic or OpenAI will IPO first putting the implied probability at 82.5% in favor of Anthropic.

The contract for the largest IPO of 2026 has SpaceX as an 83% favorite.

Microsoft (NASDAQ:MSFT) is OpenAI’s largest outside investor.

Amazon (NASDAQ:AMZN) and Alphabet (NASDAQ:GOOGL) are Anthropic’s biggest backers. All three offer public-market exposure to the AI lab race.

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